“It does,” Theo agreed.
“Do you guys think that your therapists are helping? I’ve thought of seeing a therapist, but I don’t really have a ton of money so I’m not sure if it’s worth it.”
“It’s worth it,” I said. And then I caught myself joining into a conversation that I would have preferred to stay out of. The guys looked at me and smiled, and I wasn’t sure if I was feeling terrified or relieved. I didn’t like being an open person. I didn’t love the idea of the guys knowing about my secrets. Even my therapist didn’t know about most of my secrets—I only told her what I could bear to tell her.
The room became silent again as everyone sipped their drinks.
“So thanks to those asshole jocks, we’re all a bunch of crazy virgins, huh?” Theo said with a big grin. “I guess it could be worse.” Theo took another long, deep breath. “Well, I guess one of the big reasons I wanted to see you guys this weekend was to tell you that I’m really grateful to have you as friends. You probably saved my life back in high school. I’d be lying if I said that I never considered suicide.”
“I’m right there with you,” said Ben, nodding his head.
“Same here,” said Jimmy.
But I just remained silent, inching myself closer to the fireplace as that cold shivering started to cover my whole body. I could suddenly remember those terrible days in vivid detail. I’d forgotten that the cheerleader’s name was Amanda. I could remember her taking off her skirt and wrapping it around me. She was wearing white lace panties, which were slightly sheer, so I could see her pussy. It was the first pussy I ever saw—and the only pussy I ever saw, unless you count the ones I’ve seen in pornography films.
I remembered the girls holding my legs while they waxed away my hair, one strip at a time. It hurt but I didn’t cry. They used one of those hot wax strips over my crotch. Then, Amanda dared one of the other girls to lick my cock. The other girl got down on her knees while giggling. She held up my dick and then ran the tip of her tongue from the base to the tip. Then she wiped her tongue on her shirtsleeve while saying, “Ew!” over and over. They all laughed, as if it was funny. But it wasn’t funny-jut humiliating. They were trying to make me hard, so that they could laugh and accuse me of getting hard because of the panties and the skirt.
The made me do one of their cheers, and they wouldn’t let me go until I did the whole cheer with a smile on my face. They spanked me on the ass, and then they told me they would never do it again if I gave one of the jocks a blowjob. If course I didn’t do it. I still had a tiny bit of my dignity left.
“You okay, Vinnie?” Ben asked.
I looked up from that crackling fire. “Huh—me? I’m fine,” I said, forcing a smile.
“You know, there really is something to that therapy stuff. Maybe my therapist is right—maybe it’s just a matter of embracing that stuff that happened,” Theo said.
And I couldn’t even wrap my head around what that could mean. How could I embrace those humiliating days? My mother used to drag me out of bed. I got very good at pretending to be sick, so I wouldn’t have to face those bullies, but my mom got very good at determining whether or not I was lying… Or maybe she just got good at forcing me to go to school regardless of how I felt. There were days she made me go to school while I was suffering from some terrible colds.
“How have you been embracing it?” Jimmy asked.
“I haven’t embraced it, until now,” Theo said. “I think this is a good start.”
“You know I saw that Amanda chick. I was at a bachelor party,” said Ben. “We went to a strip club and she was working the pole. She had these botched fake tits and ridiculous lip injections—and this really terrible tattoo on her back of a squid wrapped around a big rose.”
The guys started laughing. “You’re just kidding, right?” Theo asked.
“No, I’m serious. Just look up Buck-A-Roo’s. She’s on the website and everything.”
Theo had his phone out quickly. He navigated over to the Buck-A-Roo’s website and then he started to laugh. “Oh my God—that is her!” We all huddled around. And sure enough, Ben wasn’t lying. I wondered for a moment if that was where Ben secretly worked.
“Does it say her name is Princess?”
“Yeah—that’s her stage name,” Ben said. “At least it was when I was there.”
“That’s great. Isn’t Buck-A-Roo’s the one where you can go and throw loonies at the girls.”
“Yeah, that’s the one,” Ben said.
The conversation didn’t die down to a silence after that. Now the guys were excitedly trying to guess what happened to our other tormentors. I heard names that I hadn’t heard in years: Charles, Forrest, Kim, Maddy, Peter—those were the jocks and their mean cheerleader groupies. Each name made my heart skip a beat. I’d put a lot of effort into banishing those names to the depths of my mind, so they wouldn’t randomly pop up while I was trying to live my life.
Theo was looking them up on his phone, trying to see where they ended up. He found Charles’s LinkedIn page, showing that he worked at the horseracing track. Then Theo found Peter’s name in a news article. ‘Peter Smyth arrested for armed robbery, sentenced to six years in prison.’ “Look at his mug shot!” Theo said, excitedly. We all crowded the phone and laughed at Peter’s angry face.
Once that cold fear started to wear off, the night became fun again. Maybe there was something to Theo’s ‘embracing’ of our tormented pasts. Maybe this was the first step towards a proper recovery, if there could ever be one.
CHAPTER IV
It was late and I was starting to feel that long drive catching up to me when Jimmy looked at Theo and said, “So I guess it was never true then.”
And then we all looked at Jimmy and the room became silent for the first time in almost two hours. I had a feeling I knew what Jimmy was talking about, but I couldn’t say for sure. It was hard to believe that he was referring to the rumour about Theo being a cross-dressing escort in high school. Why would Jimmy, of all people, ever think that was true? It was obviously a lie started by the same people who held him down and waxed his legs and crotch.
“What’s that?” Theo asked after a long moment of hesitation.
“You know—the whole escort thing,” Jimmy said. “People said that you would dress up like a girl and sleep with guys for money. I never really believed it, but I heard one guy say that he actually saw your online profile.”
“Jimmy,” Ben said. “Just drop it.” The uppity mood of the night was suddenly crushed under the weight of the awkwardness.
“No, it’s okay,” Theo said. Then he looked down at the floor. “It’s sort of true.”
My heart stammered and my ears started ringing. I couldn’t believe what I was hearing. “Wait—what?” I said.
“I never slept with anyone. Like I said—I’m a virgin. But there was a year when my parents were struggling with the bad economy. They had to sell a few properties and it was looking like there was a chance we would have to sell pretty much everything. The bank and the government were going after my dad. He was accused of embezzlement and fraud, so he spent pretty much that whole year in court. And for that year, we were living frugally. There was no allowance and there weren’t even any birthday or Christmas presents. And after living with wealth for sixteen years, it was a hard adjustment to make. So I found a way to make a lot of money without having to miss any school, or really much time at all.”
“Wait, wait—why didn’t you just get a job at Subway after school, like I did?” Ben asked. “You’re glossing over a massive piece of this story, going from wanting some spending money to being a cross-dressing prostitute.”
“He said he never slept with anyone,” I said.
“It was just something I was good at. When I was younger, my sister would always practise her makeup on me, so I knew I could pull it off. And I just came across this website for guys who needed dates—that’s all it was: guys who needed dates for events or whatever. One of my clien
ts was just a guy who liked to eat out but he didn’t like to eat out alone. Some guys took me to movies, some guys took me bowling. One guy even flew me down to LA for a big red carpet event. I was selling myself as arm candy.”
“So these people didn’t know that you were actually a guy?”
“No, they all knew. But I was very convincing—that was the draw.”
“What?” I said. I couldn’t wrap my head around what Theo was saying.
“I think these guys were excited by the thought of bringing a tranny out with them. They liked the adrenaline boost they got when their co-workers and friends met me, wondering if people would be able to tell. I don’t really know—some of them just had fetishes. A few guys tried to sleep with me. I let one guy kiss my neck—that’s as far as it ever went.”
“I can’t believe what I’m hearing,” Ben said, shaking his head.
“Neither can I,” I said—and I really meant it. I was sure that Theo was just fucking with us. He had soft facial features, but there was no way that he could actually pass as a woman.
Theo looked at me. “You don’t believe me?” he said.
“Sorry, but I don’t. I mean—if your family was doing so bad, why do you still have this cabin? You say that your parents had to sell a few properties—but all the properties you have, you’ve had since I’ve known you.”
“This was before I knew you,” he said, as if I needed the reminder. But I still didn’t believe him. “I can prove it if you really want me to.”
And then came that silence again. The room suddenly felt cold, even though the fire had grown bigger with a new set of logs. “Okay—then prove it.”
“Vinnie,” Ben said. “Don’t make him do that.”
“I don’t mind,” Theo said as he stood up. “I’ll be back down in twenty minutes. Just keep that fire going, and feel free to open another bottle of scotch.” He walked away, up the stairs, down the hall, and into one of the upstairs rooms. We heard the door close and then we all looked at one another.
“What’s wrong with you?” Ben asked me. “You think he wants to relive that part of his life?”
“Wait—you actually believe him?” I asked.
“Of course I do. I believed it when I heard the rumours almost ten years ago.”
“You did?”
He shrugged his shoulders. “I didn’t hear it from the jocks—I heard it from the guys down in the computer lab. Everyone was talking about it. Little lies don’t gain that much traction. Though I always thought that he actually put out. I mean—who would hire a prostitute and not expect sex?”
We all looked up at the staircase. My gut turned. Was he really getting himself dolled up? And if he came down as a convincing woman, would that be enough proof to convince me? And why did he want to convince me? What was the point of all of this?
I got up and got that new bottle of scotch. I poured myself a tall glass and took a long sip, feeling that burn down in my stomach. I was on edge. I hated talking about high school. I was already dreading the next few months while these revisited memories faded back away into the depths of my mind. All of that work I did pushing those memories away was now for nothing.
It was twenty-five minutes later when Theo came down the stairs, in a dress and a pair of high heels. He had a long blonde wig on his head and a black lace choker around his throat. I stared at him for a moment and then I looked away quickly. He really did look like a woman, and I suddenly did believe his whole escort story, even though he wasn’t necessarily providing any proof.
“Wow,” Jimmy said. “You really are convincing.”
“What do you think? I clean up nicely, no?” Theo spoke with a girly voice, which was almost spot on. He did a little twirl. He was an expert on those heels, as if he really had walked down a red carpet or two.
“And you would just go out like this?” Ben asked.
Theo walked over and took a seat next to Ben. He reached his arm across Ben’s shoulders and crossed his long, smooth legs. Did he shave his legs while he was up there? Ben’s face suddenly became red. “I would go out and then we would just do stuff like this,” Theo said. “Sometimes guys just wanted a pretty girl to sit with.” He was still talking with that girly voice, which was chipping away at my fragile sanity. Theo gently began to touch Ben’s shoulder with his fingertips. “Guys liked it. Though I never really knew why.”
Ben’s face turned even redder. “I guess I can see the appeal,” he said.
“You’re so convincing,” Jimmy said for the second time in as many minutes. “How are you so convincing?”
Theo shrugged. “Practise,” he said. “I think anyone can do it—especially guys like us.”
“Guys like us?” I said. “You’re more than half a foot taller than any of us.”
“I just mean the weaker guys,” Theo said. “Guys without big muscles or chiselled Superman jawlines. As long as you’ve got a more delicate frame and a soft jawline, you can look like a chick.” Theo was still fingering Ben’s shoulder, making Ben’s face redder and redder. Ben squirmed slightly and took a deep breath. He probably wanted to jump away, but he didn’t want to embarrass himself.
“But you’ve got tits—how do you have tits?” Jimmy said, pointing directly at Theo’s chest. And I almost slapped his hand down before I remembered that he wasn’t actually pointing at a woman’s chest. Theo did have tits—how was it possible?
Theo chuckled. “It’s just some toilet paper and a bit of makeup to fake the contours of the breasts. If I was back home, I would use my Cross-Bra—it’s far more convincing than this.”
The room became silent once again while we all stared at Theo. I rubbed my eyes, thinking maybe I was just hallucinating. Maybe he didn’t really look like a chick. Maybe it was just the alcohol. How many drinks had I had? Five? Six? More than that?
“I have a crazy idea,” Jimmy said. His face was an even darker shade of red than Ben’s. We all looked over at him and waited for his crazy idea. “And it’s just an idea—maybe I’m just drunk and I’ll regret saying this in the morning, so don’t judge me too hard.”
“Out with it,” Ben said.
“What if you helped us all—you know—and then one of us could help you?”
And there was that silence again. “Help you all with what?” Theo asked.
My heart stuttered. I didn’t like where this was going.
“You know—lose our virginity. I mean—look at you. You look like a girl. You basically are a girl. So we could fuck you, and then you could fuck one of us. One of us will get dressed up tomorrow for you, and then none of us will be virgins anymore.”
Every face in that room was dark red now. There was a lump the size of a tennis ball in my throat. I tried to take a deep breath in, but even my lungs were frozen.
“That’s how my cousin lost his virginity—he was with this girl he’d been friends with and he found out she was a virgin too. They decided to just lose their virginities together, so that it wouldn’t be a burden anymore.”
“But Jimmy—Theo’s not actually a chick. She’s got no pussy to fuck,” Ben said.
“Well she looks just like a girl, so what’s the difference? There’s still a hole there, isn’t there? It’s not like we have to see her cock.”
I looked over at Theo. Why wasn’t he shutting the idea down? Why was he letting Jimmy entertain this nonsense? Theo’s lips parted but it took a moment for words to come out. “Who would do it for me tomorrow?” He looked around the room. As his gaze reached me, I looked away quickly, my heart stuttering and skipping a beat.
“We could draw straws,” Jimmy said.
“Or we could play that board game. The loser has to do it,” Ben said.
“But you have to look convincing, and you have to do the voice,” Theo said. “It’s only fair if you put in the effort as well.”
“Wait—you guys aren’t serious, are you?” I asked.
“Just think about it, Vinnie. After tonight, you won’t be a virgin anymor
e. And look at her—she’s not just convincing—she’s hot. Even you have to admit it—you aren’t going to be getting with a girl this hot anytime soon, no offense. None of us are.”
I was silent. Maybe it was the booze or maybe it was the lack of sleep, but the idea didn’t sound horrible. It sounded terrifying and crazy, but it didn’t sound horrible. I really did like the idea of ridding myself of my virginity, and Theo really did look pretty. With her long blonde hair and amazing legs—maybe it would be better than losing my virginity to some chick who had been with thirty guys before me. At least I knew Theo was clean.
“Okay. So who wants to go first?” Theo asked in that amazingly spot on girl voice.
CHAPTER V
We played Rock-Paper-Scissors to see who would get Theo’s back door first. My hand wasn’t the only one trembling when I held it out to make my play. I was up against Ben first. He threw down rock and I threw down paper. My heart trembled. I didn’t necessarily want to go first—or was it better to go first, before that hole was a sloppy mess? “Best of three,” Ben said, his voice cracking slightly. I was okay with best of three—that gave me another chance to lose.
He threw down paper and I threw down rock. We were tied with one round left. I took a deep breath and then threw down scissors. He threw down rock. A wave of relief washed over me as I took a step back.
Ben beat Jimmy, and then Jimmy beat me. So I was due to go last in the bedroom with Theo. Theo rose to her feet. She stretched out her back in a cute way and then she walked over to the nearby bedroom—the smallest of the bedrooms in the house, and the only bedroom on that first floor. He stopped in the doorway and waved Ben over with one finger. Ben rose to his feet. His legs were trembling visibly. He took a deep breath and then he disappeared into the room with Theo, leaving Jimmy and me alone.
I didn’t say anything. Jimmy was silent, too. I don’t think I could have mustered up any words if I wanted to because of that lump in my throat. We could hear the occasional creaking and squeaking coming from that closed door. I almost wished they would have gone upstairs, where we couldn’t hear them. It was a couple of minutes before I heard the muffled voice of Theo saying, “It’s so big.”
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